1-(Thien-2-ylcarbonyl)piperazine → 2-Oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-quinolin-3-carbonitrile

HRID 346646Notes

Reaction equation

HRID 346646 reaction equation
[N:1]1([C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][C:17](=[O:25])[C:16]=1[C:26]#[N:27]>C1(C)C=CC=CC=1>[O:25]=[C:17]1[C:16]([C:26]#[N:27])=[C:15]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([C:9]3[S:10][CH:11]=[CH:12][CH:13]=3)=[O:8])[CH2:2][CH2:3]2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18]1

Participants

4

Reactant 2

HCID 7975621-(Thien-2-ylcarbonyl)piperazineHCID 27775104-Chloro-1,2-dihydro-2-oxoquinoline-3-carbonitrile

Product 1

HCID 210819432-Oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-quinolin-3-carbonitrileYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Piperazine-1-yl-thiophen-2-yl-methanone (8.0 g, 41 mmol) was added to a solution of Compound 115 (4.1 g, 20 mmol) in toluene (50 mL) and heated overnight at 110° C. The solvent was removed under vacuum. The residue was suspended in water, sonicated, and filtered. The crude product was purified by flash chromatography eluting with 0–2% methanol in dichloromethane gradient to yield 6.4 g (88%) of white solids. M.P. 264° C. 1H NMR (DMSO-d6): δ 3.7 (m, 4H), 3.9 (m, 4H), 7.16 (t, J=4.8 Hz, 1H), 7.23 (t, J=5.9 Hz, 1H), 7.31 (d, J=8.6 Hz, 1H), 7.49 (d, J=4.0 Hz, 1H), 7.61 (t, J=8.3 Hz, 1H), 7.8 (m, 2H), 11.90 (b, 1H); EIMS: 364 (M+H).

Workup

  1. customThe solvent was removed under vacuum
  2. customsonicated
  3. filtrationfiltered
  4. customThe crude product was purified by flash chromatography
  5. washeluting with 0–2% methanol in dichloromethane gradient

Sources & evidence

ORD record
ord-997a2d3835b74e63ace34e99092b8d64
Source dataset
uspto-grants-2007_02
Patent number
US07173036B2

Reaction notes

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